Ethylene Glycol → Ethyl 1,4-dioxaspiro[4.5]decane-6-carboxylate

HRID 849068Notes

Reaction equation

HRID 849068 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6]1[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].[CH2:13](O)[CH2:14][OH:15].S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH+]1C=CC=CC=1>C1C=CC=CC=1>[O:15]1[C:11]2([CH2:10][CH2:9][CH2:8][CH2:7][CH:6]2[C:4]([O:3][CH2:2][CH3:1])=[O:5])[O:12][CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 336004Ethyl 1,4-dioxaspiro[4.5]decane-6-carboxylateYield 99.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To ethyl 2-cyclohexanonecarboxylate (Aldrich, 169.5 g, 1.0 mol) and ethylene glycol (Sigma, 166.7 g, 2,7 mol) in benzene (1.5 L) was added pyridinium tosylate (50.2 g, 0.2 mol). The reaction was refluxed under a nitrogen atmosphere and the water generated was removed using a Dean-Stark trap. After cooling the reaction to room temperature, half of the benzene was removed under reduced pressure and the residue was washed with 25% aqueous NaHCO3, stripped of all solvent, dissolved in CH2Cl2, dried (Na2SO4), filtered, and again stripped of all solvent under reduced pressure to provide 213 g of the title material.

Workup

  1. temperatureThe reaction was refluxed under a nitrogen atmosphere
  2. customthe water generated was removed
  3. temperatureAfter cooling
  4. customthe reaction to room temperature
  5. customhalf of the benzene was removed under reduced pressure
  6. washthe residue was washed with 25% aqueous NaHCO3
  7. dissolutiondissolved in CH2Cl2
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered

Sources & evidence

ORD record
ord-629e2ab03a9a43f9b8e36c022221eab2
Source dataset
uspto-grants-2000_01
Patent number
US06011028

Reaction notes

Loading…